67919-45-3

Upstream product

• 1811-23-0 (+)-confertifoline 
• 137644-74-7 Dithiocarbonic acid S-methyl ester O-((5S,5aS,9aS)-6,6,9a-trimethyl-4,5,5a,6,7,8,9,9a-octahydro-naphtho[1,2-c]furan-5-yl) ester 
• 137644-73-6 4,4-Dimethyl-1-prop-2-ynyloxymethyl-6,7-dihydro-4H-isobenzofuran-5-one 
• 137644-68-9 2-((5aR,9aR)-6,6-Dimethyl-5,5a,6,7,8,9-hexahydro-4H-naphtho[1,2-c]furan-9a-yl)-ethanol 
• 73878-96-3 ((S)-2-Hydroxymethyl-5,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-methanol 
• 94294-43-6 4,6,7,8,9,9a-hexahydro-6,6,9a-trimethylnaphtho<1,2-c>-furan 
• 81306-30-1 (5aR,9aR)-3-Butylsulfanyl-6,6,9a-trimethyl-1,3,4,5,5a,6,7,8,9,9a-decahydro-naphtho[1,2-c]furan 
• 58795-27-0 (S)-1,1,4a-Trimethyl-5,6-dimethylene-decahydro-naphthalene 
• 137644-62-3 C₂₀H₂₇NO₂S₂ 
• 137644-61-2 2-(6,6-Dimethyl-7-oxo-6,7,8,9-tetrahydro-4H-naphtho[1,2-c]furan-9a-yl)-N,N-dimethyl-acetamide 
• 137644-60-1 5-Hydroxy-6,6-dimethyl-4,5,8,9-tetrahydro-6H-naphtho[1,2-c]furan-7-one 
• 137644-59-8 1-Hydroxymethyl-4,4-dimethyl-6,7-dihydro-4H-isobenzofuran-5-one 
• 137644-67-8 9a-(N,N-dimethyl)carbamoylmethyl-(4,6,7,8,9,9a)-hexahydro-6,6-dimethylnaphtho<1,2-c>furan 
• 137644-78-1 (6,6-Dimethyl-6,7,8,9-tetrahydro-4H-naphtho[1,2-c]furan-9a-yl)-acetaldehyde 

Downstream Products

• 24173-70-4 11-Epivaldiviolide 
• 347423-58-9 11-epivaldiviolide 
• 218780-16-6 (+)-12α-hydroxyisodrimenin 
• 1811-23-0 (+/-)-confertifolin 
• 24173-70-4 (5aR,9aR)-1-Hydroxy-6,6,9a-trimethyl-4,5,5a,6,7,8,9,9a-octahydro-1H-naphtho[1,2-c]furan-3-one 
• 1811-23-0 (+)-confertifoline 
• 284495-73-4 3,6-dihydroxy-2-(6',6',9'a-trimethyl-4',5',5'aS,6',7',8',9',9'aS-octahydronaphtho[1,2-c]furan-3'-yl)-benzaldehyde 
• 2150-46-1 Methyl 2,5-dihydroxybenzoate 
• 490-78-8 2,5-Dihydroxyacetophenone 

Relevant academic research and scientific papers

Alternative synthetic approaches to (±)-euryfuran via the furan ring transfer reaction

Two effective synthetic approaches to (±)-euryfuran 1 are described. One synthetic route makes use of sequential furan ring transfer reaction type I and type III as key steps followed by Eschenmoser-type [3,3]sigmatropic rearrangement, and another route proceeded through furan ring transfer reaction type I and annulation with ethyl vinyl ketone subsequently.

TOTAL SYNTHESIS OF EURYFURAN VIA TWO SEQUENTIAL FURAN RING TRANSFER REACTION

Total synthesis of the marine natural product euryfuran (4) via two sequential furan ring transfer reaction is presented.Key elements of the reaction pathway include as follows; 1) the preparation of propargyl ethers (5c), (10b), and (17c), and its transformation to allylic alcohols (6), (11) and (18), 2) introduction of the angular alkyl group via sigmatropic rearrangement.

A new approach to annelated furans. The total synthesis of (+/-)-euryfuran

A new approach to annelated furans has been developed starting from ketones.Formylation of the enolate, protection of the aldehyde function as its (phenylthio)- or (n-butylthio)methylene derivative and addition of methoxy(phenylthio)methyllithium gave add

Reaction of (1S,6S)-1,7,7-Trimethyl-2,3-dimethylene-trans-bicyclodecane with Thallium(III) Acetate; a New Route to (-)-Warburganal and (+)-Euryfuran

Oxidation of the diene (2a), obtainable in two steps from manool, with thallium(III) acetate in acetic acid yielded five products.After alkaline hydrolysis they were shown on the basis of spectroscopic evidence to be (2b), (3a), (4), (5a), and (6a).These compounds may be considered as useful intermediates to naturally occurring drimanes.On oxidation with pyridinium dichromate compound (3a) afforded the aldehyde (3b), whose acetal (3c) had previously been employed in the synthesis of warburganal (7a).Oxidation of compound (4) with pyridinium chlorochromate yielded in one step the (+)-form (8) of euryfuran.

SYNTHESIS OF EURYFURAN, VALDIVIOLIDE, AND CONFERTIFOLIN

Starting from 5,5,9-trimethyl-trans-1-decalone (4), short and highly efficient synthesis of three drimane natural products, euryfuran (1), valdiviolide (2), and confertifolin (3) have been developed.